From Receptionist to CEO: Karen Kaplan’s Career at Hill Holliday

Karen Kaplan’s remarkable rise from the front desk to the corner office is proof that where you start doesn’t dictate where you’ll end up. Her 41-year journey at Hill Holliday is one of persistence, vision, and breaking through career ceilings.

Entry-Level Exec: Karen Kaplan

Karen Kaplan's career rise to CEO

Company: Hill Holliday

Started As: Receptionist

Final Role: CEO

Timeline: 1982 – 2023

Education: B.A. in French Language & Literature

Career Achievement

Under Kaplan’s leadership, Hill Holliday became one of the top advertising agencies in the country, earning a reputation for innovation and client success.

Tipping Point

Her transition from receptionist to account management marked the turning point in her career. Once given the chance, Kaplan proved she had the insight and drive to take on more strategic responsibilities.

Words to Live By

"The harder you work, the luckier you get."

Journey to the Top

Karen Kaplan joined Hill Holliday in 1982 with plans to save money for law school. She started as a receptionist, but her curiosity, work ethic, and adaptability quickly set her apart. Instead of leaving, she leaned in—taking on new challenges and exploring opportunities in account services.

T

hat pivot opened the door to a new path, and Kaplan never looked back. She steadily climbed the ranks, gaining a reputation for leadership and big-picture thinking. Over time, she became a central force in shaping the agency’s growth, reputation, and client relationships.

As CEO, Kaplan helped transform Hill Holliday into a nationally recognized agency known for bold campaigns and creative results. She led with a forward-thinking mindset while staying grounded in the values that got her there—hard work, humility, and a clear focus on people.

Her story is a reminder that no starting point is too small and that career ceilings are often meant to be broken.